CA2973330A1 - Tricyclic spiro compound - Google Patents
Tricyclic spiro compoundInfo
- Publication number
- CA2973330A1 CA2973330A1 CA2973330A CA2973330A CA2973330A1 CA 2973330 A1 CA2973330 A1 CA 2973330A1 CA 2973330 A CA2973330 A CA 2973330A CA 2973330 A CA2973330 A CA 2973330A CA 2973330 A1 CA2973330 A1 CA 2973330A1
- Authority
- CA
- Canada
- Prior art keywords
- cyano
- cyclopropan
- chromene
- phenyl
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000003413 spiro compounds Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 417
- 150000003839 salts Chemical class 0.000 claims abstract description 49
- 101150109738 Ptger4 gene Proteins 0.000 claims abstract description 38
- 239000012453 solvate Substances 0.000 claims abstract description 38
- 229940002612 prodrug Drugs 0.000 claims abstract description 36
- 239000000651 prodrug Substances 0.000 claims abstract description 36
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 35
- 201000010099 disease Diseases 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 230000004913 activation Effects 0.000 claims abstract description 20
- 230000002265 prevention Effects 0.000 claims abstract description 10
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 153
- -1 1-methyl-1-hydroxyethyl Chemical group 0.000 claims description 149
- 238000002360 preparation method Methods 0.000 claims description 145
- 238000000034 method Methods 0.000 claims description 113
- 239000002253 acid Substances 0.000 claims description 92
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 81
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 77
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 75
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 71
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 206010028980 Neoplasm Diseases 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Chemical group 0.000 claims description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 201000011510 cancer Diseases 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 230000003449 preventive effect Effects 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 150000002825 nitriles Chemical class 0.000 claims description 12
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 208000002193 Pain Diseases 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 230000036407 pain Effects 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 8
- 201000001245 periodontitis Diseases 0.000 claims description 8
- 206010009944 Colon cancer Diseases 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000003003 spiro group Chemical group 0.000 claims description 7
- 150000003536 tetrazoles Chemical class 0.000 claims description 7
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 6
- 208000020084 Bone disease Diseases 0.000 claims description 5
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- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 4
- 208000011200 Kawasaki disease Diseases 0.000 claims description 4
- 208000034486 Multi-organ failure Diseases 0.000 claims description 4
- 208000010718 Multiple Organ Failure Diseases 0.000 claims description 4
- 102000004129 N-Type Calcium Channels Human genes 0.000 claims description 4
- 108090000699 N-Type Calcium Channels Proteins 0.000 claims description 4
- 229940079156 Proteasome inhibitor Drugs 0.000 claims description 4
- 208000004680 Rectal Fistula Diseases 0.000 claims description 4
- 206010046996 Varicose vein Diseases 0.000 claims description 4
- 206010047115 Vasculitis Diseases 0.000 claims description 4
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 206010002156 anal fistula Diseases 0.000 claims description 4
- 230000000340 anti-metabolite Effects 0.000 claims description 4
- 229940100197 antimetabolite Drugs 0.000 claims description 4
- 239000002256 antimetabolite Substances 0.000 claims description 4
- 201000001883 cholelithiasis Diseases 0.000 claims description 4
- 201000010064 diabetes insipidus Diseases 0.000 claims description 4
- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 4
- 208000007565 gingivitis Diseases 0.000 claims description 4
- 239000003276 histone deacetylase inhibitor Substances 0.000 claims description 4
- 229940125697 hormonal agent Drugs 0.000 claims description 4
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 4
- 239000002955 immunomodulating agent Substances 0.000 claims description 4
- 229940121354 immunomodulator Drugs 0.000 claims description 4
- 229940043355 kinase inhibitor Drugs 0.000 claims description 4
- 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 claims description 4
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 208000003278 patent ductus arteriosus Diseases 0.000 claims description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
- 150000003058 platinum compounds Chemical class 0.000 claims description 4
- 239000003207 proteasome inhibitor Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 230000009885 systemic effect Effects 0.000 claims description 4
- 229940072172 tetracycline antibiotic Drugs 0.000 claims description 4
- 229940044693 topoisomerase inhibitor Drugs 0.000 claims description 4
- 208000027185 varicose disease Diseases 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 3
- PCCVEUAPMPIIHS-MUAVYFROSA-N 4-[4-cyano-2-[[(1'R,3S)-5-(2-methoxyethylcarbamoyl)-1,1-dimethylspiro[2H-indene-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@@H]1C[C@]11CC(C2=CC=C(C=C12)C(NCCOC)=O)(C)C PCCVEUAPMPIIHS-MUAVYFROSA-N 0.000 claims description 3
- DWUWBBZTXMNNIZ-MHECFPHRSA-N 4-[4-cyano-2-[[(1'R,3S)-5-(methylcarbamoyl)spiro[2H-1-benzofuran-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)COC1=C2C=C(C=C1)C(NC)=O DWUWBBZTXMNNIZ-MHECFPHRSA-N 0.000 claims description 3
- UDAIGVUOCPJRJV-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(propylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NCCC)=O UDAIGVUOCPJRJV-IDISGSTGSA-N 0.000 claims description 3
- FVALLBPEEPBOMY-DCFHFQCYSA-N 4-[4-cyano-2-[[(1'R,4S)-7-fluoro-6-(propan-2-ylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC(=C(C=C12)C(NC(C)C)=O)F FVALLBPEEPBOMY-DCFHFQCYSA-N 0.000 claims description 3
- 206010005003 Bladder cancer Diseases 0.000 claims description 3
- 206010005949 Bone cancer Diseases 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 208000005243 Chondrosarcoma Diseases 0.000 claims description 3
- 206010061825 Duodenal neoplasm Diseases 0.000 claims description 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims description 3
- 108090000364 Ligases Proteins 0.000 claims description 3
- 102000003960 Ligases Human genes 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 206010025323 Lymphomas Diseases 0.000 claims description 3
- 208000032271 Malignant tumor of penis Diseases 0.000 claims description 3
- 206010027406 Mesothelioma Diseases 0.000 claims description 3
- 208000034578 Multiple myelomas Diseases 0.000 claims description 3
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 3
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
- 208000002471 Penile Neoplasms Diseases 0.000 claims description 3
- 206010034299 Penile cancer Diseases 0.000 claims description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 3
- 206010039491 Sarcoma Diseases 0.000 claims description 3
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
- 206010054184 Small intestine carcinoma Diseases 0.000 claims description 3
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims description 3
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 3
- 206010057644 Testis cancer Diseases 0.000 claims description 3
- 208000023915 Ureteral Neoplasms Diseases 0.000 claims description 3
- 206010046392 Ureteric cancer Diseases 0.000 claims description 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
- 208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
- 201000005969 Uveal melanoma Diseases 0.000 claims description 3
- 206010047741 Vulval cancer Diseases 0.000 claims description 3
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 3
- 201000000312 duodenum cancer Diseases 0.000 claims description 3
- 201000004101 esophageal cancer Diseases 0.000 claims description 3
- 201000010175 gallbladder cancer Diseases 0.000 claims description 3
- 201000010536 head and neck cancer Diseases 0.000 claims description 3
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 3
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 210000000244 kidney pelvis Anatomy 0.000 claims description 3
- 208000032839 leukemia Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
- 208000020984 malignant renal pelvis neoplasm Diseases 0.000 claims description 3
- 201000002528 pancreatic cancer Diseases 0.000 claims description 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
- 239000002464 receptor antagonist Substances 0.000 claims description 3
- 229940044551 receptor antagonist Drugs 0.000 claims description 3
- 102000005962 receptors Human genes 0.000 claims description 3
- 108020003175 receptors Proteins 0.000 claims description 3
- 201000007444 renal pelvis carcinoma Diseases 0.000 claims description 3
- 201000000849 skin cancer Diseases 0.000 claims description 3
- 230000004936 stimulating effect Effects 0.000 claims description 3
- 201000003120 testicular cancer Diseases 0.000 claims description 3
- 208000008732 thymoma Diseases 0.000 claims description 3
- 201000011294 ureter cancer Diseases 0.000 claims description 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
- 206010046766 uterine cancer Diseases 0.000 claims description 3
- 206010046885 vaginal cancer Diseases 0.000 claims description 3
- 208000013139 vaginal neoplasm Diseases 0.000 claims description 3
- 201000005102 vulva cancer Diseases 0.000 claims description 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 2
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 2
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 2
- 239000003972 antineoplastic antibiotic Substances 0.000 claims description 2
- 229940125400 channel inhibitor Drugs 0.000 claims description 2
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical group C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 229940121372 histone deacetylase inhibitor Drugs 0.000 claims description 2
- 230000002584 immunomodulator Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- YOTUXJLJJYNCDG-CUNXSJBXSA-N 4-[4-cyano-2-[[(1'R,3R)-5-(2-methoxyethylcarbamoyl)spiro[1,2-dihydroindene-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@@H]1C[C@]11CCC2=CC=C(C=C12)C(NCCOC)=O YOTUXJLJJYNCDG-CUNXSJBXSA-N 0.000 claims 1
- XLVIQYDVJGLHGQ-CPJSRVTESA-N 4-[4-cyano-2-[[(1'R,3R)-5-(methylcarbamoyl)spiro[1,2-dihydroindene-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@@H]1C[C@]11CCC2=CC=C(C=C12)C(NC)=O XLVIQYDVJGLHGQ-CPJSRVTESA-N 0.000 claims 1
- ILHOIEZMIAPIJM-KDYSTLNUSA-N 4-[4-cyano-2-[[(1'R,3S)-1,1-dimethyl-5-(methylcarbamoyl)spiro[2H-indene-3,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@@H]1C[C@]11CC(C2=CC=C(C=C12)C(NC)=O)(C)C ILHOIEZMIAPIJM-KDYSTLNUSA-N 0.000 claims 1
- YVFQNCXSOKGUTA-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(1,3-oxazol-2-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1OC=CN=1 YVFQNCXSOKGUTA-FNZWTVRRSA-N 0.000 claims 1
- LCBYYQCHPYAMAA-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(1-methyltriazol-4-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1N=NN(C=1)C LCBYYQCHPYAMAA-FNZWTVRRSA-N 0.000 claims 1
- VUYVAYGJSMJMLO-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(2-methoxyethylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NCCOC)=O VUYVAYGJSMJMLO-IDISGSTGSA-N 0.000 claims 1
- DFIFIZUBBHPKMN-KMRXNPHXSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1OC(=NN=1)C1CC1 DFIFIZUBBHPKMN-KMRXNPHXSA-N 0.000 claims 1
- BATIOXOHZJUKRZ-IADCTJSHSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(6-methoxypyridin-3-yl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1C=NC(=CC=1)OC BATIOXOHZJUKRZ-IADCTJSHSA-N 0.000 claims 1
- VBKGXTLRBXXGGA-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(cyclopropylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC1CC1)=O VBKGXTLRBXXGGA-IDISGSTGSA-N 0.000 claims 1
- XYOOKHABSDFNLY-DWACAAAGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(cyclopropylmethylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NCC1CC1)=O XYOOKHABSDFNLY-DWACAAAGSA-N 0.000 claims 1
- MULMVPWPRFNYIF-FNZWTVRRSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(ethylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NCC)=O MULMVPWPRFNYIF-FNZWTVRRSA-N 0.000 claims 1
- QSRLBYGDVFRMPT-IDISGSTGSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(propan-2-ylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC(C)C)=O QSRLBYGDVFRMPT-IDISGSTGSA-N 0.000 claims 1
- ZUTDVAODKSCPLI-KMRXNPHXSA-N 4-[4-cyano-2-[[(1'R,4S)-6-(pyridazin-3-ylcarbamoyl)spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC=1N=NC=CC=1)=O ZUTDVAODKSCPLI-KMRXNPHXSA-N 0.000 claims 1
- KKCSSZHLXPTZJP-KMRXNPHXSA-N 4-[4-cyano-2-[[(1'R,4S)-6-[(1-methylpyrazol-3-yl)carbamoyl]spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C(NC1=NN(C=C1)C)=O KKCSSZHLXPTZJP-KMRXNPHXSA-N 0.000 claims 1
- SXBCGSNJVIIQCT-IADCTJSHSA-N 4-[4-cyano-2-[[(1'R,4S)-6-[6-(methylamino)pyridin-3-yl]spiro[2,3-dihydrochromene-4,2'-cyclopropane]-1'-carbonyl]amino]phenyl]butanoic acid Chemical compound C(#N)C1=CC(=C(C=C1)CCCC(=O)O)NC(=O)[C@H]1[C@]2(C1)CCOC1=CC=C(C=C12)C=1C=NC(=CC=1)NC SXBCGSNJVIIQCT-IADCTJSHSA-N 0.000 claims 1
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CR20180323A (es) | 2015-11-20 | 2018-08-06 | Idorsia Pharmaceuticals Ltd | Derivados de indol n-sustituídos como moduladores de los receptores de pge2 |
TWI795362B (zh) * | 2016-07-07 | 2023-03-11 | 日商小野藥品工業股份有限公司 | 拮抗藥與免疫核查點阻礙藥而成之組合 |
EA201992677A1 (ru) | 2017-05-18 | 2020-04-23 | Идорсия Фармасьютиклз Лтд | Пиримидиновые производные в качестве модуляторов pge2 рецепторов |
CA3063632A1 (en) | 2017-05-18 | 2018-11-22 | Idorsia Pharmaceuticals Ltd | Benzofurane and benzothiophene derivatives as pge2 receptor modulators |
LT3625222T (lt) | 2017-05-18 | 2021-11-10 | Idorsia Pharmaceuticals Ltd | Fenilo dariniai, kaip pge2 receptoriaus moduliatoriai |
CA3063637A1 (en) | 2017-05-18 | 2018-11-22 | Idorsia Pharmaceuticals Ltd | N-substituted indole derivatives |
ES2896476T3 (es) | 2017-05-18 | 2022-02-24 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina |
JP7211358B2 (ja) * | 2017-05-22 | 2023-01-24 | 小野薬品工業株式会社 | Ep4アンタゴニスト |
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CN112300019A (zh) * | 2019-07-31 | 2021-02-02 | 华东师范大学 | 一种邻乙酰氨基苯丁酸类化合物的制备方法 |
EP4245301A1 (en) | 2020-11-13 | 2023-09-20 | ONO Pharmaceutical Co., Ltd. | Cancer treatment by combined use of ep4 antagonist and immune checkpoint inhibitor |
JP2024016314A (ja) * | 2020-12-24 | 2024-02-07 | 小野薬品工業株式会社 | 一般式(i-a)で示される化合物、その薬学的に許容される塩、またはそれらの水和物と免疫チェックポイント阻害薬および/またはep4受容体拮抗薬との組み合わせ |
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CA2081679A1 (en) * | 1991-11-27 | 1993-05-28 | Raj N. Misra | Gem-dialkyl-7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease |
US6242493B1 (en) * | 1998-03-13 | 2001-06-05 | Merck Frosst Canada & Co. | Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment |
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AU756333B2 (en) * | 1998-03-13 | 2003-01-09 | Merck Frosst Canada & Co. | Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment |
US6211197B1 (en) * | 1998-10-07 | 2001-04-03 | Merck Frosst Canada & Co. | Prostaglandin receptor ligands |
AU2001278771A1 (en) * | 2000-08-22 | 2002-03-04 | Ono Pharmaceutical Co. Ltd. | Carboxylic acid derivatives, process for producing the same and drugs containingthe same as the active ingredient |
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WO2004037247A1 (en) * | 2002-10-21 | 2004-05-06 | Irm Llc | Oxindoles with anti-hiv activity |
UA80474C2 (en) * | 2003-02-26 | 2007-09-25 | Sugen Inc | Aminoheteroaryl compounds as inhibitors of protein kinase |
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WO2013090552A1 (en) | 2011-12-13 | 2013-06-20 | Yale University | Compositions and methods for reducing ctl exhaustion |
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2018
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